Miles From Tomorrowland: First Time's The Charm
by TheDailyRabbit
Summary: Rated M for explicit sexual content. Miles confronts his first erection with the help of his mother as he moves into puberty. Later, Loretta gets some help as well.
1. Chapter 1: Miles' First

Hello Everybody,

I know it's been a really, really fucking long time since anything was ever heard from me. No, I haven't dropped off the face of the earth, I've just been really really fucking busy. SO. Over the next few weeks, I'll be pushing out more chapters for everything. Hopefully. But for now, I'll leave this request here. This story is a request from none other than my one of my greatest patrons, commenters, and readers, adrpad44. To adrpad, I'm sorry it took so long but incest is hard to write, ok? So here you go. I hope you can forgive the length of time.

As far as tags and ratings go, this is gonna be a real fast, hard, M for mature. Gracious depictions of sex, incest, etc. So if you are uncomfortable reading a sexfic about miles and his momma, leave now.

Miles sat bolt upright in bed, his throbbing erection waking him from an otherwise peaceful slumber. He'd never had a stiffy before, and it hurt. So he did what any kid would do: run to his momma and explain what was wrong. Running down the hall on the dormitory level of the Stelosphere, he nearly crashed into the potted plant outside his parents' room, diving through the door and into the bed. His father had already woken up, or hadn't slept at all last night, fixing something broken somewhere on the massive spacecraft. So he landed in the empty spot on the bed and rolled into his mother's waiting arms. "Good morning miles," Phoebe Callisto greeted the over-excited boy. "'Morning Mom!" Miles exclaimed. He rolled onto his stomach to face her; big mistake. As he rolled, his knob planted itself like a pole-vaulter's staff into the bed, and he groaned in sudden agony before his knob dislodged itself and he completed his roll, returning to his back once again. Phoebe looked down. '_my my, someone hasn't learned how to deal with _that_ yet. I thought Leo was supposed to talk to him about that._' "So, first time stiffy huh?" she questioned her son.

"Yeah. I woke up and my stuff was hard and sore. Pleeeeeeease mom, can you fix me?"

"Miles, there's nothing wrong with you. This is just part of growing up. Even dad had to deal with that sometimes. And I was going to have him talk to you about it, but he's busy right now so I guess I'll do it. Get out of bed, and we'll see what we can do."

Miles sat up and got out of his mothers' bed, waiting for her to make him feel all better. She changed her clothes in the closet quickly, then walked to the door. Leaving the room, she beckoned Miles to follow, and he did, closing the door to the room as he left. Leading him through the more _disused _passages in the ship, they eventually stopped outside the med bay. "Ok, come on in and we'll have you feeling better in no time." So miles walked in. as the door hissed shut behind him, he felt something microscopic and very sharp prick his neck. He turned to the left and saw his mother standing with a hypodermic injector in her hand, its payload vial empty. Suddenly he felt his cock harden once more, this time to an almost inconceivable point. It was so erect and sore that he almost crumpled over, his head dropping low and his voice crying out in pain. He started ripping and tearing at his clothes, successfully losing his shirt. He crumpled more; his mother pulled his pants down and off, before helping him stand. But he fell over as his little-protected baby arm collided with the exam table. Pulling his boxers down and off his legs, his mother quickly lifted him onto the surgical table and strapped him down, doing up the webbing restraints around his head, midsection, arms, and legs. His legs, she moved to the sides bringing him to a full split. His arms she laid out in a straight line perpendicular to his head. And finally she popped a gel mouthpiece into his mouth, "To prevent you from biting your own tongue off and choking on it," she explained.

What Miles hadn't noticed was that his mother had changed into doctors' scrubs. As she gloved up, he wondered how being strapped down with his poor knob straight into the air would help him. Phoebe started assembling supplies on a tray, before wheeling over the tray and a stool to the table. Her 3mm green nitrile exam gloves sparkled slightly as she hovered over his erect shaft. She drew a measuring tape from the tray. Measuring his cock, she noticed that it stood at a rather respectable 4 and 1/3rd inches long, with a girth of just over an inch. She then blindfolded her son, stating, "This part, you might not want to watch." She lifted another syringe and an alcohol swab and cleaned the skin just above his dick, below his waistline. She then injected him with a sedative/relaxant mixture. The mixture made Miles feel very lightheaded and limp. Next, Phoebe picked up a 2" speculum, lubed it, and slowly inserted it into Miles' ass. Then, she lubed a ¼" sound and began to sound Miles' small penis with it. He then began to feel his dick get very tight. He then felt his mother place an oxygen mask over his nose. As he inhaled, he felt even lighter and softer than before. His mother returned to her task of bringing down his erection. She opened the speculum and gaped Miles' ass wide, wide enough to get her whole hand inside him. And she did; she reached in with her left hand and placed a small electro-stim vibrator pad directly on the area near his prostate. She then activated the gravitic field and Miles was lifted off the table, still strapped to the padding that held him to a steel board that served as the bottom of the table connected to the legs. He was then flipped upside down but felt nothing. He waited patiently as his cock continued to tighten and throb gently as his mother sounded his dick and let his ass be vibrated and electrocuted. Once his balls started to contract after about fifteen minutes of sounding, Phoebe removed the 1/2-inch sound she was using from his urethra and placed a cock pump over his, well, cock. She pumped the bulb attached to the pump until his dick was an inch longer and he could feel it through the painkillers. For the final acct, she then turned the electrodes in the vibrator in his ass up to full strength, set the vibrate function on high, and continued to pump his cock. With her free hand, she felt his balls to make sure he wasn't too close to cumming. Once he was mere seconds away, she rapidly released the pressure from the pump and put the collection sleeve over his dick. She then grabbed a cattle prod and jabbed it into his ass, pressed down hard on his prostate, and set it off. The resulting electric shock, combined with the downforce being exerted on his prostate, the rhythm of the vibrator, and the cock sleeve set Miles off, his cum blasting up his urethra into the collection sleeve. He shot one, two, three, then 6, 7, then 9, 10, and finally, 12 bursts of hot sticky jizz into the sleeve before passing out on the table. As she removed the various tools and things from in and around his body, Phoebe had a thought: _I've got to try this with Loretta some time._ She carried Miles back to his room, set him in bed gently, and then went to take a shower.

That's all for this chapter. Part 2 features Loretta, and comes out tomorrow. Bye all!


	2. Chapter 2: Loretta's Awakening

Well everyone, here's chapter two of the fic requested at some point in time by adrpad44. This second chapter isn't part of the original request, it's a continuation idea that came from myself.

Rated M for more graphic sexual content.

Chapter 2: Loretta's Awakening

A few days after the med-bay event, Miles and Loretta were chatting casually over a game of chess. Being siblings wasn't easy, and even more so in space. However, they trusted each other and helped each other when it really counted. Which is how Loretta found out about the med-bay event. It happened casually, as she moved a rook into place and took one of Miles' pawns. "Mom did something with me the other day," Miles started casually. "Oh really?" answered Loretta, a bit of scorn in her voice.

"Yeah but it was in the med-bay." Miles replied. That stopped Loretta cold. No one "did anything" in the Med-bay for any reason other than actual medical treatments. Intrigued, she continued to play the game without thinking, focusing on questioning Miles. "And what did she do?" Loretta asked.

"She did this thing with me that made me super sleepy and then she put something in my… butt." Miles held off on the last word, making Loretta both scared and interested. As a Pubescent teenage girl, Loretta was prone to mood swings, terrible anger, strange feelings of attraction and lust, and she was ready to make good on some of those things. "Show me."

"Eww. No!"

"Well, how am I supposed to believe you if I can't see it for real?"

"Ask mom to do it for you."

"That's a fair idea, actually." Moving her knight, she put Miles in check. He dodged out by castling, but Loretta swooped her bishop in and put Miles in check mate. "I win."

"Nice move. I forgot your bishop was so close by." Loretta turned off the holographic chess set and shook her brother's hand, then left for the kitchen to grab a snack.

Three days later…

Loretta woke up from a particularly unrestful night and went to wash and dress for the day. As she sat down to relieve herself, she discovered that she was bleeding. She immediately screamed for her mother, who hurtled into the room at top speed, almost tripping over her daughter in the process. Upon hearing the explanation of the situation at hand, Phoebe immediately took charge, urging her daughter to dress and come to the medical bay when she was done. Once finished, Loretta made her way to the medical bay, unaware of what exactly awaited her. Her mother was already in doctor's scrubs, setting up equipment trays, as Loretta came inside. "Sweetie, change into that gown. Take everything off underneath." Her mother instructed, pointing to the gown set out on the exam table. Loretta took the gown and entered the restroom, stripping in private and coming out wearing the gown with a neatly folded pile of her clothes in hand. "Hop up, dear" her mother instructed. Loretta climbed onto the table and laid down, the pain in her gut obvious and stunning for the young brunette. Her mother gently palpated her stomach, massaging her waist to ease the pain.

She eventually picked up a hypodermic injector and loaded it with sedative, before plunging it into Loretta's neck. The teenager's eyes began to relax from their tightly shut position as the sedative took over. Her body became less rigid and more at ease, and her mother blindfolded her, put an oxygen mask on her face, and strapped her down. For Loretta, she didn't know what would happen, but she didn't care. The pain that hounded her crotch and made her bleed was far away, like it was happening to someone else as she watched. Phoebe donned green gloves and rolled over a stool, two instrument trays, and a portable heating pad. She placed the warm pad on Loretta's stomach, tucking it in under the straps to keep it secure. Flicking on the large overhead surgical lamps, she withdrew a speculum and lube from the trays and slowly inserted a lubricated speculum into her daughter's young vagina, spreading her labia wide to expose her clitoris, urethra, and vaginal walls. Slipping her hands away, she went to the trays once more and came up with a sterile catheter, which she slipped into Loretta's bladder. Draining her daughter's bladder into a collection bag, she set it on the table and got to work, administering a pain-reducing drug with the hypo-injector into Loretta's arm. She turned on the nitrous oxide gas flow, further relaxing her daughter. Phoebe then inserted another speculum into Loretta, this time into her asshole. Gaping it wide, she sawed at it with her fingers, before putting her whole hand into her daughter's ass. Stretching the opening, she withdrew her hand and slid in the same huge butt plug that Miles had gotten. Phoebe inspected her subject.

She decided from personal experience that her daughter needed to orgasm, so she pulled out the speculums, and pushed a vibrating dildo into Loretta's cunt. As she turned the vibrator up to max strength, Loretta could feel fire in her gut even through the sedatives and howled through the mask. She finally came, shaking the table. Her mother cleaned her up, bathed her, and put her back in her bed, letting her daughter sleep it off.

And that's it. If you have any story ideas you would like me to work on, please PM me. I know I've been very inconsistent as of lately, and writers' block and university are the main culprits. I'm free of block now, so I can crank through it. Let me know if you're interested in seeing a specific story!

Thanks,

TheDailyRabbit


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